Uracil → 1-allyluracil

Participants

Reaction Conditions

Reaction Steps

2.5 g (104 mmol, 80% suspension) of NaH was added to a suspension of 10.5 g (93 mmol) uracil in 100 ml DMF and the reaction allowed to continue for 2 hours at room temperature. After 2 hours 10.73 mL (15 g, 123 mmol) allylbromide was added and the mixture heated for 2 hours at 70° C. The solvent was removed under reduced pressure and the residue treated with methylene chloride. The residue from the methylene chloride extract was a mixture of mono-allyl- and di-allyl-uracil. 5.5 g (39%) of 1-allyluracil was isolated by preparative column chromatography, using chlormoform/methanol 40:1 as eluant (m.p. 108–109° C., Lit. 105–109° C., Beilstein).

Provenance & Evidence